Sr Director, Sr Real Estate Counsel

Tailored Brands is a leading specialty retailer of menswear, including suits, formalwear, sportswear, and a broad selection of business casual offerings. Our brands include Men's Wearhouse, Jos. A. Bank, Moores and K&G Fashion Superstore , which offers merchandise for the entire family. We help people love the way they look and feel for their most important moments by delivering personalized products and services through our convenient network of stores and e-commerce sites.
About the Job
We currently have an exciting opportunity for an attorney to join our Corporate Legal team as Sr Director, Sr Real Estate Counsel. This individual will be responsible for legal aspects of Tailored Brands' retail store real estate portfolio and lead a team of Real Estate Counsel supporting lease transactions across the U.S. and Canada.
What You’ll Do

- Lead and manage the Company's real estate legal function, overseeing all legal aspects of the retail store portfolio, including new leases, amendments, renewals, assignments, subleases, and terminations across the U.S. and Canada.

- Draft, review, and negotiate commercial leases, letters of intent, amendments, and related real estate agreements directly with landlords, brokers, and outside counsel, ensuring terms align with Company standards and protect Company interests (e.g., exclusive use, co-tenancy, and kick-out remedies).

- Manage lease negotiations to closing within established timing expectations, driving accountability for initial comments, redlines, and draft turnaround.

- Supervise, coach, and manage the workload of the Real Estate Counsel team, reviewing work product, setting timing expectations, and holding the team accountable for quality and on-time delivery.

- Partner closely with the SVP, Real Estate & Construction and Real Estate Directors on deal strategy, lease structure, and portfolio decisions to support store growth, relocations, remodels, and closures.

- Maintain accurate, up-to-date lease files and status reporting (e.g., document status logs, deal recaps), proactively flagging timing risk or landlord issues to leadership.

- Advise on lease disputes, landlord defaults, and other real estate legal matters in coordination with the broader Legal Department.

- Partner with cross-functional business teams, including Construction, Store Operations, and Finance, to support real estate transactions and portfolio initiatives.

- Manage outside counsel on real estate matters as needed, with an eye toward driving business goals while effectively managing time and cost.

What You’ll Bring

- Juris Doctor (JD) from an accredited law school

- Membership in good standing with at least one U.S. State Bar

- 10+ years of legal experience in commercial real estate, with substantial experience in retail leasing (in-house and/or law firm)

- Demonstrated experience independently negotiating and closing commercial leases, amendments, and related real estate agreements

- People management experience, with the ability to lead, coach, and hold a team accountable for quality and timely work product

- Strong organizational skills and the ability to manage a high-volume portfolio of active lease matters simultaneously

- Excellent written, oral, and interpersonal communication skills, with the ability to build effective relationships with landlords, brokers, and internal business partners

- Sound business judgment and the ability to balance legal risk with business needs in a fast-paced retail environment

- Proficiency with contract lifecycle management (CLM) tools and lease administration systems a plus

Please note that you do not need to qualify for all requirements to be considered. We encourage you to apply if you can meet most of the requirements and are comfortable opening a dialog to be considered.
Work Environment, Physical & Mental Demands

- Ability to sit and work at a computer keyboard for extended periods of time

- Ability to stoop, kneel, bend at the waist, and r